Potassium Carbonate → N,N'-bis-(2,6-diisopropylphenyl)-N"-(4-bromomethylphenyl) methylguanidine

HRID 5758Notes

Reaction equation

HRID 5758 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([NH:16][C:17]1[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=1[CH:26]([CH3:28])[CH3:27])=[NH:15])([CH3:3])[CH3:2].[Br:29][CH:30](Br)[C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:23]([C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:26]([CH3:28])[CH3:27])[C:17]=1[NH:16][C:14]([NH:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11])=[N:15][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][Br:29])=[CH:32][CH:33]=1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124904871-(Dibromomethyl)-4-methylbenzeneHCID 178418589HCID 178418589, compound

Product 1

HCID 86747216N,N'-bis-(2,6-diisopropylphenyl)-N"-(4-bromomethylphenyl) methylguanidineYield 39.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

11.4 g (0.03 mole) of N,N'-bis-(2,6-diisopropylphenyl) guanidine, 8.7 g (0.03 mole) of α,α-dibromo-p-xylene and 2.1 g (0.015 mole) of anhydrous potassium carbonate were added to 50 ml of toluene. The thus-formed mixture was then refluxed under heating for 10 hours. After the mixture had been allowed to cool, the insoluble substance was removed by filtration. The thus-obtained filtrate was washed with water and the concentrated for the purpose of recovering the solvent to obtain a slightly brown powder. The powder was then recrystallized from acetone to obtain 6.6 g of white powder.

Workup

  1. temperatureThe thus-formed mixture was then refluxed
  2. temperatureunder heating for 10 hours
  3. temperatureto cool
  4. customthe insoluble substance was removed by filtration
  5. washThe thus-obtained filtrate was washed with water
  6. concentrationthe concentrated for the purpose
  7. customof recovering the solvent
  8. customto obtain a slightly brown powder
  9. customThe powder was then recrystallized from acetone

Sources & evidence

ORD record
ord-da0c1141ff4a4a2e80f2daaa6a47cc27
Source dataset
uspto-grants-1993_09
Patent number
US05246810

Reaction notes

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